Chiral Discrimination through 1 H NMR and Luminescence Spectroscopy: Dynamic Processes and Solid Strip for Chiral Recognition

2017 ◽  
Vol 23 (72) ◽  
pp. 18303-18313 ◽  
Author(s):  
Monalisa Gangopadhyay ◽  
Arunava Maity ◽  
Ananta Dey ◽  
P. R. Rajamohanan ◽  
Sapna Ravindranathan ◽  
...  
Keyword(s):  
Chiral Recognition ◽  
Chiral Discrimination ◽  
Luminescence Spectroscopy ◽  
Dynamic Processes ◽  
H Nmr

Enantioselective Recognition of Chiral Guests by the Water-Soluble Chiral Keplerate {Mo132} Spherical Capsule with 30 Inner Lactate Ligands

2019 ◽  
Author(s):  
Nancy Watfa ◽  
Weimin Xuan ◽  
Zoe Sinclair ◽  
Robert Pow ◽  
Yousef Abul-Haija ◽  
...  
Keyword(s):  
Aqueous Solution ◽  
Chiral Recognition ◽  
Association Constants ◽  
Water Soluble ◽  
Enantioselective Recognition ◽  
H Nmr ◽  
Dosy Nmr ◽  
Spherical Capsule ◽  
Surface Pores ◽  
Guest Chemistry

Investigations of chiral host guest chemistry are important to explore recognition in confined environments. Here, by synthesizing water-soluble chiral porous nanocapsule based on the inorganic metal-oxo Keplerate-type cluster, {Mo<sub>132</sub>} with chiral lactate ligands with the composition [Mo<sub>132</sub>O<sub>372</sub>(H<sub>2</sub>O)<sub>72</sub>(<i>x-</i>Lactate)<sub>30</sub>]<sup>42-</sup> (<i>x</i> = D or L), it was possible to study the interaction with a chiral guest, L/D-carnitine and (<i>R</i>/<i>S</i>)-2-butanol in aqueous solution. The enantioselective recognition was studied by quantitative <sup>1</sup>H NMR and <sup>1</sup>H DOSY NMR which highlighted that the chiral recognition is regulated by two distinct sites. Differences in the association constants (K) of L- and D-carnitine, which, due to their charge, are generally restricted from entering the interior of the host, are observed, indicating that their recognition predominantly occurs at the surface pores of the structure. Conversely, a larger difference in association constants (K<i><sub>S</sub></i>/K<i><sub>R</sub></i> = 3) is observed for recognition within the capsule interior of (<i>R</i>)- and (<i>S</i>)-2-butanol.

ChemInform Abstract: Chiral Discrimination of Fructo-Oligosaccharides Toward Amino Acid Derivatives by Induced-Fitting Chiral Recognition.

ChemInform ◽  
2010 ◽  
Vol 32 (32) ◽  
pp. no-no
Author(s):  
Motohiro Shizuma ◽  
Hiroshi Adachi ◽  
Mishio Kawamura ◽  
Yoshio Takai ◽  
Tokuji Takeda ◽  
...  
Keyword(s):  
Amino Acid ◽  
Chiral Recognition ◽  
Chiral Discrimination ◽  
Amino Acid Derivatives

Optical nanoprobes for chiral discrimination

The Analyst ◽  
2020 ◽  
Vol 145 (20) ◽  
pp. 6416-6434
Author(s):  
Arafeh Bigdeli ◽  
Forough Ghasemi ◽  
Nafiseh Fahimi-Kashani ◽  
Samira Abbasi-Moayed ◽  
Afsaneh Orouji ◽  
...  
Keyword(s):  
Chiral Recognition ◽  
Chiral Discrimination ◽  
Sensing Systems ◽  
Optical Nanoprobes ◽  
Luminescent Sensing

Chiral recognition can be achieved by exploiting chiral properties of nanoparticles within various colorimetric and luminescent sensing systems.

A novel electrochemical chiral sensor for 3,4-dihydroxyphenylalanine based on the combination of single-walled carbon nanotubes, sulfuric acid and square wave voltammetry

The Analyst ◽  
2014 ◽  
Vol 139 (9) ◽  
pp. 2243-2248 ◽  
Author(s):  
Lisha Chen ◽  
Fengxia Chang ◽  
Lingchen Meng ◽  
Meixian Li ◽  
Zhiwei Zhu
Keyword(s):  
Carbon Nanotubes ◽  
Sulfuric Acid ◽  
Chiral Recognition ◽  
Square Wave Voltammetry ◽  
Single Walled Carbon Nanotubes ◽  
Chiral Discrimination ◽  
Square Wave ◽  
Single Walled Carbon ◽  
Wave Voltammetry ◽  
Walled Carbon Nanotubes

The combination of SWV with chiral SWCNTs and H2SO4 shows chiral discrimination for 3,4-dihydroxyphenylalanine, and the three are indispensable for this chiral recognition.

A bisthiourea-based 1 H NMR chiral sensor for chiral discrimination of a variety of chiral compounds

2016 ◽  
Vol 231 ◽  
pp. 129-134 ◽  
Author(s):  
Guangling Bian ◽  
Shiwei Yang ◽  
Huayin Huang ◽  
Hua Zong ◽  
Ling Song
Keyword(s):  
Chiral Discrimination ◽  
Chiral Compounds ◽  
H Nmr

Exploring Dynamics and Stereochemistry in Mechanically-Interlocked Compounds

2005 ◽  
Vol 70 (10) ◽  
pp. 1493-1576 ◽  
Author(s):  
Scott A. Vignon ◽  
J. Fraser Stoddart
Keyword(s):  
Self Assembly ◽  
Structural Changes ◽  
Variable Temperature ◽  
Molecular Switches ◽  
Dynamic Processes ◽  
Condensed Phases ◽  
H Nmr ◽  
Structural Types ◽  
Solution Dynamics ◽  
Stereochemical Properties

The advent of self-assembly and template-directed synthetic protocols has led to a tremendous surge in the number of mechanically-interlocked compounds being prepared and studied. As these investigations are being carried out, it is becoming increasingly apparent that many of these compounds, known as catenanes and rotaxanes, possess unique dynamic and stereochemical properties. In addition, the drive to create molecular switches and machines for nanotechnological applications has generated a need to understand how to control those properties in condensed phases. Here, we present an overview of the field with regard to the solution dynamics and stereochemistry of mechanically-interlocked compounds - as well as to some related structural types - and review the recent results from our own research in some detail. 1H NMR spectroscopy has proven to be a powerful tool for probing both degenerate and nondegenerate dynamic processes in these compounds, as well as for identifying stereoisomers if they are present in solution. The results of several variable temperature NMR investigations on the effects of structural changes upon the dynamic processes and stimulated relative motions of components in catenanes and rotaxanes, as well as in some self-complexes and pretzelanes, are discussed. A review with 90 references.

scholarly journals Recognition and Sensing of Chiral Organic Molecules by Chiral Porphyrinoids: A Review

Chemosensors ◽  
2021 ◽  
Vol 9 (8) ◽  
pp. 204
Author(s):  
Gabriele Travagliante ◽  
Massimiliano Gaeta ◽  
Roberto Purrello ◽  
Alessandro D’Urso
Keyword(s):  
Scientific Community ◽  
Chiral Recognition ◽  
Organic Molecules ◽  
Chiral Discrimination ◽  
Spectroscopic Techniques ◽  
Chiral Molecules ◽  
Relevant Research ◽  
Non Covalent Interactions ◽  
Organic Guests ◽  
Covalent Interactions

Porphyrinoids are extremely attractive for their electronic, optical, and coordination properties as well as for their versatile substitution at meso/β-positions. All these features allow porphyrinoids to behave as chiroptical hosts for chiral recognition by means of non-covalent interactions towards chiral guests. Over the years, chiral discrimination of chiral molecules such as amino acids, alcohols, amines, hydroxy-carboxylic acids, etc. has aroused the interest of the scientific community. Hence, this review aims to report on the progress to date by illustrating some relevant research regarding the chiral recognition of a multitude of chiral organic guests through several chiral mono- and bis-porphyrins via different spectroscopic techniques.

Effect of Tartaric Acid on the Electrochemical Behavior of K3[Fe(CN)6] on the Electrodes Coated with Cyclodextrin Modified Multi-Walled Carbon Nanotubes

2013 ◽  
Vol 781-784 ◽  
pp. 346-351
Author(s):  
Hai Tao Wang ◽  
Shi Zhao Kang ◽  
Qiu Ling Yang ◽  
Jin Mu
Keyword(s):  
Carbon Nanotubes ◽  
Tartaric Acid ◽  
Electrochemical Behavior ◽  
Chiral Recognition ◽  
Electrochemical Reaction ◽  
Chiral Discrimination ◽  
Molecular Chirality ◽  
Control Step ◽  
Multi Walled Carbon Nanotubes ◽  
Walled Carbon Nanotubes

The effect of tartaric acid on the electrochemical behavior of K3[Fe(CN)6] was investigated on bare ITO electrodes, electrodes coated with multi-walled carbon nanotubes possessing carboxyl groups (MWNT-COOHs), and electrodes coated with cyclodextrin modified multi-walled carbon nanotubes (MWNT-CDs), respectively. It is found that the molecular chirality of tartaric acid can hardly influence the electrochemical behavior of K3[Fe(CN)6] on bare ITO electrodes. When the electrodes coated with MWNT-COOHs are used, the effect of the molecular chirality becomes distinguish. In the case of the electrodes coated with MWNT-CDs, the enhanced chiral discrimination between D-tartaric acid (D-TA) and L-tartaric acid (L-TA) can be observed. The control step in the electrochemical reaction of K3[Fe(CN)6] on the electrodes coated with MWNT-CDs is deduced to be different when D-TA or L-TA is introduced into the solution, respectively. Therefore, the enhanced chiral discrimination on the electrodes coated with MWNT-CDs is probably due to the change of the control step in the electrochemical reaction of K3[Fe(CN)6] caused by the chiral recognition of cyclodextrin moieties to D-TA and L-TA.

On the applicability of functional-group symmetry-adapted perturbation theory and other partitioning models for chiral recognition – the case of popular drug molecules interacting with chiral phases

2019 ◽  
Vol 21 (40) ◽  
pp. 22491-22510
Author(s):  
Michał Chojecki ◽  
Dorota Rutkowska-Zbik ◽  
Tatiana Korona
Keyword(s):  
Perturbation Theory ◽  
Interaction Energy ◽  
Chiral Recognition ◽  
Functional Group ◽  
Chiral Discrimination ◽  
Group Symmetry ◽  
Intermolecular Interaction Energy ◽  
Drug Molecules ◽  
Chiral Phases ◽  
Interacting Quantum Atoms

The F-SAPT partitioning of the intermolecular interaction energy, supported with the Interacting-Quantum-Atoms analysis, is a powerful tool for studies of the origin of chiral discrimination within diastereoisomeric complexes of the RR and RS types.

Enantioselective fluorescent sensors for chiral carboxylates based on BINOL — Synthesis and chiral recognition

2010 ◽  
Vol 88 (4) ◽  
pp. 367-374 ◽  
Author(s):  
Kuo-xi Xu ◽  
Yu-xia Wang ◽  
Shu-yan Jiao ◽  
Jin Zhao ◽  
Chao-jie Wang
Keyword(s):  
Nmr Spectroscopy ◽  
Chiral Recognition ◽  
Fluorescent Sensors ◽  
Enantioselective Recognition ◽  
H Nmr ◽  
Recognition Ability ◽  
Chiral Materials ◽  
Fluorescent Recognition ◽  
Derivatives Of ◽  
C Nmr

The four novel derivatives of 1,1′-bi-2-naphthol (BINOL) have been prepared, and the structures of these compounds have been characterized by IR, MS, 1H and 13C NMR spectroscopy, and elemental analysis. The enantioselective recognition of these receptors has been studied by fluorescence titration and 1H NMR spectroscopy. The receptors exhibited different chiral-recognition abilities towards some enantiomers of chiral materials and formed 1:1 complexes between host and guest. The receptors exhibit excellent enantioselective fluorescent-recognition ability towards the amino acid derivatives.

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